How Chili Piper Used AI to Hit $40m Revenue, Turn Profitable with Co-Founder Alina Vandenberghe

Tim founded SaaS Group in 2018 using his own money from Eyeo exit to acquire Deploybot. SaaS Group is structured as an LLC and funded all deals with equity until 2020 when they began using debt. In 2024, they sold about 5% of the SaaS Group LLC for $25m implying a value of $500m. They’ve purchased 20 companies over the last 5 years. Their companies do $60m in combined revenue today and employ 300 people. They typically pay 2-4x multiples. DashThis, Usersnap, and Rewardful are some of their larger companies. Can they acquire $60m more in ARR over the next 12 months?

How ActiveCampaign hit $100m ARR on way to $300m

Alessandro Chesser was one of the leading sales executives at Carta for 7 years. They always talked about helping Founders set up Trusts to preserve wealth - but it never launched. In February of 2022 he left to launch Dynasty and make the Trust process easier for Founders. Why South Dakota? Revocable or Irrevocable? 0% tax or 40% tax? We talk about it all live. 

Tyler Denk launched Beehiiv after missing out on the ""Founder Money"" the MorningBrew team made when they exited. Today, his tool helps newsletter creators launch, grow, and monetize. The firm did $1.5m in revenue last month split between SaaS, ad revenue, and kickbacks on cross promoting newsletters. Can they hit $25m ARR this year?

She bootstrapped to $12m in revenue in under 18 months. Rebecca Shostak launched FloDesk.com in 2017 as an email marketing tool focused on beautiful design for solopreneurs. As of May 2024, 80,000 customers pay $28/mo on average and the firm just launched their second product: Sales funnels. She's done this all with a team of just 50 people - $540k in revenue per employee. Will she break $35m in ARR this year and remain bootstrapped?

Inside Beamer acquiring UserFlow and creating a $10,000,000 revenue machine. Userflow had no reason to sell with 50% EBITDA margins, 650 customers and completely bootstrapped. How did Beamer, using Camber fund money, get the deal done?

Sam Jacobs launched Pavilion in 2019 to help sales reps learn. Today, he does $11m in annual revenues and has expanded to CEO's, CMO's and other leadership groups. Can they hit $15m in revenue before Dec 2024?

Owner.com is a $20m ARR SaaS for restaurants that had F90 day churn of 30% before Kyle Norton joined as CRO. He fired 4 AE’s, narrowed the ICP focus, and got burn multiple down from 1.2x to 0.8x as they hit $6m in ARR. Today they do $20m. Can they break $25m before Dec 2024?

The idea that AI can save you cost and help you reach profitability might be a good one. Chili Piper hit $40m in revenue and profitability as Alina built AI into more parts of the org. Here's how she did it across customers, ecosystem, and employees.